title: Straightforward synthesis of non-natural L-chalcogen and L-diselenide N-Boc-protected-γ-amino acid derivatives.
abstract: The synthesis of new chiral seleno-, telluro-, and thio-N-Boc-γ-amino acids is described herein. These new compounds were prepared through a simple and short synthetic route, from the inexpensive and commercially-available amino acid L-glutamic acid. The products, with a highly modular character, were obtained in good to excellent yields, via hydrolysis of chalcogen pyroglutamic derivatives with overall retention of the L-glutamic acid stereochemistry. Also, an L-diselenide-N-Boc-γ-amino acid was prepared in good yield. This new synthetic route represents an efficient method for preparing new L-chalcogen- and L-diselenide-γ-amino acids with biological potential.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil.
authors.forename: Cristiane Y
authors.initials: CY
authors.lastname: Kawasoko
authors.forename: Patricia
authors.initials: P
authors.lastname: Foletto
authors.forename: Oscar E D
authors.initials: OE
authors.lastname: Rodrigues
authors.forename: Luciano
authors.initials: L
authors.lastname: Dornelles
authors.forename: Ricardo S
authors.initials: RS
authors.lastname: Schwab
authors.forename: Antonio L
authors.initials: AL
authors.lastname: Braga
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018011:Chalcogens / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D018011:Chalcogens; D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; C473453:seleninic acid